Tranny
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So this is the story about how I got my first experience being a bottom, and why it was with a tranny.I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...
For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall slim tranny sitting...
For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall, slim tranny sitting...
I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.In August 2007 I was 24...
I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn’t get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...
I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn't get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...
My Wife and I have been married for about 3 years now and have since recently, been looking to have our first experience with a she male. I met a girl online name Judy and after chatting for a while and exchanging pictures we agreed to a meet and greet. Judy proved to be a very sexy transgender with feminine features. Her highlighted hair was long and she had size B cup breast with a thick firm ass and long pretty legs. She was very beautiful and had an awesome personality. We sat down and...
She MalesSo this is the story about how i got my first experience being a bottom, and why it was with a trannyI was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...
I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the...
Dreams can be strange, sexy things. Your wife may be a stunning knock-out, way the fuck out of your league, but I bet she ain’t your dream girl. No, your perfect fantasy angel has the big tits and pretty face you love so much, but she’s also got something extra: a big ol’ dick between her legs. Sorry, wifey, but tonight may be a good evening to spend with DreamTranny.DreamTranny.com is a site with history. They’ve been around since 2000, making them one of the older shemale porn operations on...
Premium Shemale Porn SitesSo I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here.So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago with a hot black tranny named Jade and her friend. I quickly found a very nice 20 something tranny names Maria who said I would do. We went through a few chat sessions, with our cams on and I convinced...
While I was in the military, there were many opportunities to see some of the wild and crazy sites and people of the world. One time in Japan a bunch of us in a mixed group (men and women) went to a show that featured transsexuals. These were men who now dressed and acted like women. All of the men/women featured had breast implants to additionally make you believe they were real. The show was very exciting with each of the trannies on stage showing us they were as good looking without their...
I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog for a beautiful woman. I must admit, I've jerked off more than a few times to shemale porn on my computer at home, wondering what it would...
So since I got a good rating for my first sex story, I shall write another one about my first time with a tranny. This happened last year. She was 25, and I was 21. So I am Ash, I am 22, I pretty good and masculine looking. I am mostly a bottom though. I have always been a huge fan of shemales and ladyboys. Respect them and also lust for them :p anyway, so I was in dubai last year and I thought that there might be much more shemales and easier to meet since the place was quite forward with a...
Gay MaleRevenge on a Tranny My relationship with my partner Julie had been strained over the last twoof our ten years together. For a period of six months we?d stopped having sex.I thought she might leave me but I figured that if she was going to find anotherwoman then there was nothing I could do about it and besides, I had a womanor two I knew I could fall back on for affection if I ever found the need.I was a good lover, but there seemed to be something that Julie needed sexuallythat I couldn?t...
-------------------------------------------------------------------------- I went to Alan's house after work one day to talk to him. His mom was single and she need a male figure to discuss masturbation since she had caught him doing it. I rang the bell. I heard footsteps on the stairs and then the door opened. "Hi Alan." "Oh, hi Mr. Jones." “Can i come in?” “Sure,” he said holding the door open. “Alan I have to be home soon, so let me just say this quickly: I know your mom caught...
Jermaine Simpson drove his white 2010 Peterbilt raised-roof big rig into the truck stop just outside of the city. He called his friend, Mariah.“Hey, baby,” the dark-skinned transsexual answered.“What’s up boo? I’m at the truck stop,” Jermaine shared.“Okay, oool! I’m on my way.”“Awesome! Can I get a shower at your house?”“Of course!”“See you in a few.”“Bet!”Jermaine’s nine-and-a-half-incher was already hard. He loved fucking her whenever he was down this way. Once he had taken her on a six-day...
Garvey Williams kissed the pretty, effeminate, white boy he had had been secretly fucking since they were high school sophomores. Back then, Garvey was a standout wide receiver with high prospects of moving on to Division One. He had progressed as everyone thought and Jamie Collier, the femboi, followed him to the large state university. Garvey and the Mustangs earned a national championship his junior year. The football prodigy decided that he should enter the NFL draft immediately following...
I have always been considered a strong athletic straight black man. I have fucked a plenty of women being an executive in a high profile position. I had everything a man could ask for Power, Property and Plenty of Pussy. Well in life, all things change. I had just landed another two million dollar client and was out celebrating with friends over a local bar. I was feeling real good and I never believed in going home alone…..so why should tonight be different. Then after a few or too many drinks...
She MalesI'm your run of the mill middle-aged white guy; divorced, decent job, plenty of hobbies, and your standard list of perversions. I love women. I love the way they smell, I love their bodies, I love their personalities, and I really love having sex with them. I've had a few bisexual encounters in my day, mostly back in college, and while I have no phobias about man-on-man action, I have never been attracted to the same sex. Although admittedly, the sight of a large, erect cock has always made my...
It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place. What was I doing in here? In truth I did not know but I was 16, horny and wanted to find out about the rumours about sexual activity. I was still a virgin and although had messed around wanking at home, I was very naïve. I walked into the last cubicle, shut and bolted the door, took...
It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place.What was I doing in here? In truth I did not know but I was 16, horny and wanted to find out about the rumours about sexual activity.I was still a virgin and although had messed around wanking at home, I was very naïve.I walked into the last cubicle, shut and bolted the door, took my...
This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my family have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I...
This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my family have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I...
I’d been single for a few months and having the shittyist of luck on dating sites. I was unemployed and making some deliveries to the gay community for some extra cash. One of my regular stops was to a tranny named Tory she wasn’t bad looking and she never made a move on me other than asking if I’d like to hangout for a few minutes. Anyway I’d seen her on one of the chat rooms on a dating site... now I’d been without sex for at least a few weeks and I got a little curious. I started...
My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits. We dated for about a month when talk her into just taking her shirt off, after a while without her shirt off she finally took her bra off. I would make out with her and suck on her tits, lick her...
We went in her room, I paid her and while I was getting undressed, she was waiting for me by the bed. She was slowly stroking her cock, and didn't bother to remove her panties or lace body suit. She just moved them aside and pulled out her cock and boobs.She was tall, at least 180cm, latina, slim, hot, long dark hair big boobs and nice and big cock, (later when she was hard, she was probably 18-20cm). She didn't speak English, but she was so hot and I was so horny, ready to make my fantasy come...
I had been alone for a while and I was really horny. I am not the best looking guy but cute and a little over weight. I am 6'1" tall and about 280. So going to a bar was not going to work so I started to search craigslist for some one. I found a couple women but after emailing them I found out they all wanted me to join some web site and I was not looking for that. So I kept looking and I found a woman who was real and interested in me after we exchanged emails. So I set a date with her to get...
My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met a tranylicous. We Started to chat. I remember going to the profile on the side of the message window and I found out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address. it was not to far from Downtown so I head over to meet her as I smoked a joint. She had a nice apt, pretty empty She had just moved from Ny. After a little chat we had that helped me relax She came...
[i[/i]im donnie, i had just dropped my girlfriend of at shipyard to work graveyard shift. i wanted to have a drink in bar, not a beer in a parking lot. as i drove toward the bridge i saw a cocktail sign, u know a cocktail glass. so i made my way to that street and pulled up in front of "the black rose". i went in and sat at the bar and ordered shot of jack and a bud. ik looked around and thought i died and went to heaven. all i saw was tits and leg and pretty women. i was enjoying the view...
My name is Holly, and I'm twenty-eight. I'm a blonde, and I happen to be a lesbian. I have been with a couple guys before, but that's it. Anyway, one night, I was at a club securing the perimeter. Looking for some cute ladies, that maybe I'd take home. I saw a lot of worthy candidates, and a couple with D-cup racks. I wasn't a slut or anything like that, but I definitely played the field. I looked around the entire club a few times, and caught a few eyes. I saw a few ladies casually stirring...
TransI met Charkara (her real name) through an adult dating site. You can find her pictures on my xhamster page titled, "My First Tranny". We corresponded through the dating site quite regularly before we decided to take it to next level and exchange phone numbers and email addresses. We talked on the phone getting to know each other, what we liked to do sexually, etc. She came off as a total freak willing to do most anything which was an extreme turn-on for me. We then begun having phone sex...
The Truck Driver and the Tranny fiction by [email protected] This is a work of fiction for mature readers, containing explicit sexual acts which may be illegal in some backward parts of the world. If it's illegal where you're reading it, you should MOVE! If you're too young to be reading erotic and explicit sexual fiction, don't go any further. I was working as a truck driver, moving periodically to new areas of the country (mostly around my hometown of Nashville, TN) in...
FUCKING MY FIRST TRANNYIn the early to mid 90's my wife and I were living in south central L.A. The wife wasn't necessarily a sexual creature nor was she very good at it. This lead me to a lot porn watching and going outside of the house for hot, kinky sex. She doesn't know I'm Bi and still doesn't to this day. I would frequent various adult bookstores to get/give blowjobs, handjobs and visit the occasional gloryhole to get my freak on. I would also travel up and down Figueroa or more commonly...
As I headed toward the office, I could see the pool, and immediately thought about taking a swim after checking in. After getting my room key, I decided to cut through the pool area. It was a large pool for a hotel, there were plenty of chairs, and it looked very clean and inviting. Casually looking around, there were only a few people, and as I continued toward the other end where my room was, there was an attractive younger lady that caught my eye. She was laying on one of the loungers by...
Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry.Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...
Love StoriesMe again, I haven't shared any of my stories in a while but was chatting to an old friend about this one last week and thought I would share the story. Again names have been changed to protect identity, all my stories are true and I am not a author, just a horny guy with some horny stories. Thanks.I was 20 years old and had been playing with guys and gals for many years now (check old stories). I had arranged a night out with some of my friends to celebrate a birthday so put on my new shirt,...
I’ve been talking to this woman for awhile. After our steamy car make out session I was hooked. I didn’t care if she had a dick. I wanted more of her. It was clear that she wanted more from me. We texted non stop everyday. It was fun. She blew up my phone with loads of naked selfies. I’d sit and admire her beautiful body. With every picture she’d send, my dick would throb with excitement. She would even ask if videos of me masterbating to her pictures haha she was amazing. whenever I worked...
When Father Mortimer checked into the hotel it was eight in the evening.The room was a basic no frills double with a small bathroom. He would never stay in such a hotel if he was attending one of his ecclesiastical conferences but for what he had planned it was just perfect.He got down on his knees and bent his balding aged head over a black gilt leaf Bible he had respectfully placed on the edge of the bed.“Blessed Lord Jesus forgive me for my sins,” he muttered and crossed himself three...
SpankingGrowing up in the neighborhood we all had a thing for Mrs. Jansen. Besides the fact that she was unbelievably sweet, she was also drop dead gorgeous. I would often find myself staring at her sunbathe in the afternoon and would often fantasize about her before I go to bed.With Mr Jansen working many hours I would always offer to help Mrs Jansen with some things around the house like carry heavy boxes, rake the yard, and move her furniture around. During my junior year, I was eager to go to the...
There is nothing more hot than to have a slim, pretty body on my hands to fondle. To feel their erections starting to grow and to taste their cocks in my mouth. I lose control when I'm around a shemale.I have fantasized a lot about getting fucked for long periods of time and in a lot of different positions. Unfortunately, all my shemale hookups have been with escorts that do the deeds rather quickly and then leave. I still have to find a shemale friend to spend long long hours either fucking,...
I was bored one day so i decided to rent out a transsexual escort. I called her up so we can do a special photo shoot together and needless to say, we ended up fucking. She came to my door with an all black dress on and the sides were transparent. She had 5 inch open toe heels on and a leather jacket that came to her waist. Her hair was long and curly and she was fair skinned and spanish about 5'8 with heels on. She walked in and asked me where i wanted to start. I pointed to the couch and she...
I would never go out looking for it, I'm a good girl. But I would never avoid it. After all, just being dressed in black inch-mesh fishnets, held up by suspenders from a black lacy basque, nipped hard at my waist, with my cock-clit barely covered by my pink g-string pouch and the string over my divine snow white left cheek, while I tottered about on 8", platform heeled, "fuck-me" shoes, and nothing ...
My name is Holly, and I’m twenty-eight. I’m a blonde, and I happen to be a lesbian. I have been with a couple guys before, but that’s it. Anyway, one night, I was at a club securing the perimeter. Looking for some cute ladies, that maybe I’d take home. I saw a lot of worthy candidates, and a couple with D-cup racks. I wasn’t a slut or anything like that, but I definitely played the field. I looked around the entire club a few times, and caught a few eyes. I saw a few ladies casually stirring...
I was horny as fuck that day as I hadn’t jizzed in a few days due to work being so hectic. I debated how to get my rocks off and decided to go cruising at the park for some cock. I took a quick shower, threw on a pair of pink frilly panties, a pair of loose sport shorts, and a long tshirt. I hopped in my car and drove to the park, teasing my little prick by rubbing it in my sissy panties, leaking copious amounts of precum into them as a result. I parked and headed towards the wooded area...
It was laundry day. Vincent, or Vinnie to his friends, loved laundry day. It was a time to relax, catch up on reading, and listen to music while the washing machines whirred in the background.He was tall and ruggedly handsome, with dark, almost Spanish features. In his five or so years of living alone, he always cherished his trips to the laundromat.Walking slowly from his house to the laundromat, he whistled a tune. In his little trolley, he had his laundry and detergent. Sitting on top of his...
TransAt first I didn’t like that my wife, Jan, was hanging out with a “guy” several times per month. She insisted, however, that her friend “Crystal” was actually a girl trapped in a man’s body — and as such was attracted to men. Since she posed no sexual threat, she enjoyed their time together because they shop and talk and hangout without expectations. To be fair, my wife had a soft spot for gay men - she’s had numerous gay friends over the 8 years we’ve been together. Crystal (formerly Chris) was...
TranssexualIt was a typical Saturday morning. I was at the grocery store doing my weekly food shopping. As I was perusing through the vegetable section my eyes caught sight of a a very attractive woman. She had long dark brown hair, pretty face and a nice body. I worked my way over to her and checked her left hand for a wedding ring. She had none. I made some remarks about the slim pickings the supermarket had. She and I quickly engaged in conversation about cooking etc.We walked around the store side by...
So I woke this morning in a particularly aroused state, I decided I would treat myself some naughty fun, I decided to dress like a slut under my work clothes. I rummaged around in my drawer and pulled out some black seamed nylons, black lace panties and and my favourite lace corset. I began by showering and shaving my whole body, once I had finished I began by rolling the smooth nylons on to my smooth muscular legs, then came the lace corset followed by the small lace panties, I then reached...
I was horny as fuck that day as I hadn't jizzed in a few days due to work being so hectic. I debated how to get my rocks off and decided to go cruising at the park for some cock. I took a quick shower, threw on a pair of pink frilly panties, a pair of loose sport shorts, and a long tshirt. I hopped in my car and drove to the park, teasing my little prick by rubbing it in my sissy panties, leaking copious amounts of precum into them as a result. I parked and headed towards the wooded area...
It was a typical Saturday morning. I was at the grocery store doing my weekly food shopping. As I was perusing through the vegetable section my eyes caught sight of a a very attractive woman. She had long dark brown hair, pretty face and a nice body. I worked my way over to her and checked her left hand for a wedding ring. She had none. I made some remarks about the slim pickings the supermarket had. She and I quickly engaged in conversation about cooking etc.We walked around the store side by...
A little something different to spice up your lives*******************************************************************************************************************************************************************************************It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go...
Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking lot. There were several men beating up a beautiful woman, when I tried to break it up I ended up getting very banged up myself. Her name was misty, she thanked me for helping her and asked if I need a...
I had been on this sex dating site for only a few weeks, when I got a request to meet from phillip, I looked at his profile and it read 25 year old single male, looking for older women, sexual orientation-straight,I thought to myself , should I tell him? No fuck it let him find out for himself.So I arranged a meet with phil for the following day at 2pm,I douched, showered, took my time putting on make-up, dressed , did my hair (wig) and nails, although I say it myself I looked hot, not slutty...
I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty horney since my doctor is a female and I had a complete physical so she and her nurse were in the room with me. I got to the train station to go back to Willow Grove and was standing on the platform when I saw this beautiful brunette haired woman about 10 feet from me. She was wearing jeans, and a spagetti top shirt. I could see that she had a real nice pair of tits and my cock started to get hard...
THE AMAZING MR. MORTIMER My girlfriend Rachel and I had decided to take a two week vacation to PuertoRico. I had first come across the girl on the streets of San Juan. She cameup to me and begged me for some money. At first I was going to say no. ThenI noticed how beautiful this young girl was and I was intrigued. I startedto reach into my purse to get her something, and she smiled at me. She hada very beautiful smile. It was in fact an entrancing smile. I kept her close to me with small bribes...
Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry. Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...
As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...